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“Several billionaires got their first stakes in
poker games. Kirk Kerkorian funded his first business, the
charter airline Los Angeles Air Service, with poker winnings.
H.L. Hunt bet everything he had in a poker game and won his first
oil well. Bill Gates, John Kluge, Texas oil mogul Clint
Murchison, and corporate raider Carl Icahn all played poker for
large stakes before they got rich. It’s not just billionaires:
Richard Nixon paid for his first congressional campaign with
poker winnings and parlayed that into the presidency, where he
continued to make risky bets but with less success. History is
filled with people who began their routes to success with
gambling winnings. You won’t find as many equally successful
people whose first stake was a bank loan or money raised from
issuing securities. Even the losers can benefit. Writers from
Dostoyevsky to Mario Puzo credited gambling losses for both the
inspiration and the motivation to complete some of their greatest
works.”

Barring the inheritance of a substantial family fortune — or
being handed the reins of an extremely lucrative business — it is
hard to become exceptionally wealthy without taking aggressive
calculated risks. Knowing how to position for upside while
managing the downside is thus a highly desirable skillset.

In that light, why might poker figure prominently in the
biographies of billionaires? Did the game hone and shape their
instincts… or did their natures instinctively draw them to the
game… or both?

Calculated risk is the mother’s milk of poker and trading —
two zero sum (actually minus sum) games in which variance
dominates short term, but skill dominates long term.

Do you remember the last aggressive calculated risk you took?
Do you think about trading in these terms?